Tetrabutylammonium Fluoride → 4-(2-Cyclopropylindol-1-yl)cyclohexanol

HRID 1092418노트

반응식

HRID 1092418 반응식
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH:24]2[CH2:26][CH2:25]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:24]1([C:16]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]3)[C:23]3[C:18]([CH:17]=2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:26][CH2:25]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 576757611-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole

생성물 1

HCID 576757584-(2-Cyclopropylindol-1-yl)cyclohexanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Crude 1-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole from above (10.4 mmol) was dissolved in tetrahydrofuran (150 mL), and tetrabutylammonium fluoride (21 mL, 1 M in THF, 21 mmol) was added. After the reaction was stirred for 72 hours it was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), concentrated and purified by SiO2 chromatography (10-50% ethyl acetate/hexanes) to give two (cis/trans) isomers (355 mg of the more polar isomer, 681 mg of the less polar isomer) of the desired alcohol. LC-MS (C17H21NO calc'd 255) m/z 256 (M+H).

후처리

  1. concentrationwas concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (10-50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-dceffded7f8246fea9a9f201c4b9b2f8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129424B2

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